The title compound, also referred to as methyl-2-deoxyriboside (MDR), is a ribofuranose derivative that has traditionally been prepared by acid-catalyzed methanolysis of 2-deoxy-D-ribose (2DR).
MDR may be used as a starting material for the production of 2DR derivatives, useful as intermediates in many pharmaceutical synthesis applications.
During the formation of MDR, a significant amount of the pyranose isomer (3R,4S)-6-methoxytetrahydro-2H-pyran-3,4-diol, also referred to as methyl-2- deoxyribopyranoside (MDRP), is generated along with the desired product.
MDRP generates pyranose impurities in derivatives prepared from the MDR, and therefore it is desirable to remove it prior to preparing such derivatives. For example, the use of sodium periodate to remove MDRP by oxidation is described by R. K. Ness et al., The Journey of Organic Chemistry, 1961, Vol. 26, No. 8, pp. 2895-2899. The oxidation is carried out in an aqueous medium that is buffered with phosphate to pH 6.4-6.8, apparently to protect the acid sensitive methoxy group at position 1. The complicated workup procedure involves the use of ion exchangers to remove periodate oxidation products. Simpler and more easily scalable methods of removing MDRP from MDR would therefore benefit the pharmaceutical industry.